trans-Zeatin

trans-Zeatin Basic information
Product Name:trans-Zeatin
Synonyms:(e)-2-buten-1-o;(E)-Zeatin;2-Buten-1-ol,2-methyl-4-(purin-6-ylamino)-,(E)-;ZEATIN, CRYSTALLIZED;TRANS-6-(4-HYDROXY-3-METHYLBUT-2-ENYLAMINO)PURINE(ZEATIN);TRANS-ZEATIN [TRANS-6-(4-HYDROXY-3-METHYLBUT-2-ENYLAMINO)PURINE];(2E)-2-METHYL-4-(1H PURIN-6-YLAMINO)-2-BUTEN-1-OL;2-Buten-1-ol, 2-methyl-4-(1H-purin-6-ylamino)-, (2E)-
CAS:1637-39-4
MF:C10H13N5O
MW:219.24
EINECS:605-343-5
Product Categories:Biochemistry;Cytokinins;Purine;PLANT GROWTH REGULATOR;Plant Growth Regulators;Plant Hormones;Miscellaneous Natural Products;Amines;Bases & Related Reagents;Heterocycles;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Nucleotides;Inhibitors;Pharmaceuticals;plantgrowth;Elisa Kit-plant ELISA Kit
Mol File:1637-39-4.mol
trans-Zeatin Structure
trans-Zeatin Chemical Properties
Melting point 207 °C
Boiling point 395.0±52.0 °C(Predicted)
density 1.40±0.1 g/cm3(Predicted)
storage temp. -20°C
solubility H2O: soluble
pka14.77±0.10(Predicted)
form powder
color off-white to yellow
Merck 14,10117
BRN 616241
CAS DataBase Reference1637-39-4(CAS DataBase Reference)
EPA Substance Registry SystemZeatin (1637-39-4)
Safety Information
Hazard Codes Xi
Safety Statements 22-24/25
WGK Germany 3
RTECS EM9506000
8-10-23
HS Code 29335990
Hazardous Substances Data1637-39-4(Hazardous Substances Data)
MSDS Information
ProviderLanguage
trans-Zeatin English
ACROS English
SigmaAldrich English
trans-Zeatin Usage And Synthesis
Descriptiontrans-Zeatin is a cytokinin plant growth regulator with antioxidant and neuroprotective activities. It binds to the cytokinin receptor Arabidopsis histidine kinase 3 (AHK3) with a KD value of 1.3 nM. trans-Zeatin increases chlorophyll levels in etiolated Cucumus sativus cotyledons in a concentration-dependent manner. It increases callus growth and shoot formation in N. tabacum calluses when used at concentrations of 5 and 50 μM. trans-Zeatin (25-100 μM) reduces production of reactive oxygen species (ROS) induced by amyloid β (25-35) (Aβ25-35) in PC12 cells. It reduces scopolamine-induced spontaneous alternations in the Y-maze, indicating enhanced spatial memory, in mice when administered at doses of 1.5, 3, and 4.5 mg/kg per day.
Chemical Propertieswhite to light yellow crystal powder
Physical properties Trans-zeatin is freely soluble in acetic acid and water.
UsesLabelled Zeatin. It is purified from Zea mays, is a member of the cytokinin group of plant growth factors, the activity of which is attributed to its more stable trans form -induced matrix metalloproteinase-1 expression via MAP kinase signaling in human skin fibroblasts. Trans-Zeatin is a potential agent for the management of skin photoaging.
UsesZeatin, purified from Zea mays, is a member of the cytokinin group of plant growth factors, the activity of which is attributed to its more stable trans form metalloproteinase-1 expression via MAP kinase signaling in human skin fibroblasts. Trans-Zeatin is a potential agent for the management of skin photoaging.
UsesZeatin, purified from Zea mays, is a member of the cytokinin group of plant growth factors, the activity of which is attributed to its more stable trans form. Trans-Zeatin inhibits UVB-induced matrix metalloproteinase-1 expression via MAP kinase signaling in human skin fibroblasts. Trans-Zeatin is a potential agent for the management of skin photoaging.
DefinitionChEBI: The trans-isomer of zeatin.
General Descriptiontrans-Zeatin contains a hydroxylated isoprenoid side chain.
Biochem/physiol ActionsZeatin upon reduction forms zeatin O-glucoside, which is widely present in plants. It possesses transportation and storage functions, along with defence against zeatin oxidases.
Purification MethodsPurify zeatin by recrystallisation from EtOH or H2O. The UV has max at 207 and 275nm ( 1,400 and 14,650) in 0.1N aqueous HCl; 212 and 270nm ( 17,050 and 16,150) in aqueous buffer pH 7.2; 220 and 276nm ( 15,900 and 14,650) in 0.1N aqueous NaOH. The picrate has m 192-194o (from H2O) from which zeatin can be recovered by treatment with Dowex-1 x 8 (200-400 mesh, OH-form). [Letham et al. Aust J Chem 22 205 1969, Proc Chem Soc (London) 230 1964, Shaw & Wilson Proc Chem Soc (London) 231 1964.] It is a cell division factor (plant growth regulator) [Letham & Palni Ann Rev Plant Physiol 34 163 1983] and inhibits mitochondrial function [Miller Plant Physiol 69 1274 1982]. The commercially available trans -9-riboside derivative, [6025-53-2], M 351.4,is a cytokine which separates from aqueous AcOH with m 177-179o. It solubility in AcOH is ~5%. [McDonald & Morris Methods Enzymol 100 347 1985].
trans-Zeatin Preparation Products And Raw materials
Raw materials1H-Isoindole-1,3(2H)-dione, 2-[(2E)-4-(acetyloxy)-3-methyl-2-buten-1-yl]-
trans-Zeatin-riboside Methylparaben Methyl TRANSFAT Bensulfuron methyl Trans-Zeatin Amino tris(methylene phosphonic acid) Kresoxim-methyl Purine 5-Amino-2-methylpyridine trans,trans-2,4-Undecadienal Tris(hydroxymethyl)aminomethane Methyl salicylate Methyl bromide CHLOROPHOSPHONAZO III METSULFURON METHYL METHYLCYCLOPENTADIENE DIMER N,N-Dimethyl-1,4-phenylenediamine

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